Thomas Hollis, FRS, FSA, was a political philosopher, philanthropist, dilettante and traveller of republican sympathies, whom Wilson painted in Rome in 1752 (P43 Portrait of Thomas Hollis, Harvard Art Museums/Fogg Museum, Harvard University). He had been trained in public service and spent the years from 1740 to 1748 practising law. He toured Europe twice (1748-49 and 1750-53), mixing with French philosophes and Italian artists including Piranesi. He was an admirer of Cromwell, Milton and Algernon Sidney, an ardent advocate of colonial rights and one of the architects of American independence. He was also a major collector of books, medals, engravings and classical antiques, as well as a patron of Canaletto and Wilson. He presented books to the libraries of Harvard, Berne and Zurich universities.

When painted by Wilson, Hollis was travelling with his friend and heir, Thomas Brand (c.1717-1770), who in 1753 was painted by Thomas Jenkins. It was through their work for Brand and Hollis that Wilson's and Jenkins's relationship developed.Hollis went on to purchase from Wilson 'A landscape of the Grotto in Villa Madama, called Il Teatro near Rome ... Painted on the spot in the open air, by R. Wilson, 1752 for T.H.' (John Disney, Memoirs of Thomas Brand-Hollis, Esq., London, 1808). In addition he bought an unidentified view of Lake Albano. On 26 October, 1761, after his return to London, Hollis recorded in his diary: 'Mr Wilson, the Landscape Painter breakfasted with me, and thanked me handsomely for having presented a Landskip picture of his, which I had bought at Capt. Hamilton's sale of pictures for £10.10 to the British Museum'. The painting in question was P46 Ariccia I, Tate London (Wilson and Europe 2014, pp. 77, 86, n. 84).